Tetrahydrofuran → (S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-one

HRID 1014728Notes

Reaction equation

HRID 1014728 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12](Br)[CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[C:25](Br)[C:24]([N+]([O-])=O)=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1([C@@H](N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>C(OCC)(=O)C>[C:1]1([C@@H:7]([N:9]2[C:10]3[CH:11]=[C:12]([C:43]4[CH:42]=[CH:41][CH:40]=[C:23]5[C:24]=4[CH:25]=[CH:26][CH:21]=[N:22]5)[N:13]=[CH:14][C:15]=3[NH:16][C:50]2=[O:49])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 758181-Phenethylamine, (-)-HCID 81531DiisopropylethylamineHCID 160998502,4-Dibromo-5-nitropyridineHCID 86626410((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine

Product 1

HCID 24984682(S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-oneYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine. To a solution containing 2,4-dibromo-5-nitropyridine (500 mg, 1.75 mmol) and diisopropylethylamine (314 uL, 1.80 mmol) in tetrahydrofuran (8 mL) at 0° C. was added (S)-(−)-1-phenylethylamine (225 mg, 1.86 mmol). The reaction was allowed to come to room temperature and stirred for 18 h. The reaction was complete via LCMS and the solution was condensed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated to give the desired product (5.6 g, 99%). MS (ESI) m/z 322 [M+1]+.

Workup

  1. customto come to room temperature
  2. customcondensed under reduced pressure
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2788e98dbc28453c81283d0a3e3d6f05
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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